Reaktion #6295

Reaktionsgleichung

4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

aniline

toluenesulfonic acid

methacrylic acid

4-nitrophenylacetic acid

→

4-(N-2-hydroxyethyl-N-ethylamino)-4'-nitro-1,4-diphenyl-1,3-butadiene

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture then is heated
2. 2
   Temperaturat reflux for 16 hours
3. 3
   TemperaturAfter cooling to room temperature
4. 4
   Sonstigethe solid diphenylbutadiene precipitates from solution
5. 5
   Filtrationis collected by filtration
6. 6
   Sonstigepurified by recrystallization from ethanol

Vorschrift

A solution of 21.9 g (0.1 mole) of 4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde, 9.3 g (1 mole) of aniline, and 0.19 g (1 mole %) of toluenesulfonic acid in toluene is heated at reflux for 17 hours with azeotropic removal of water. After the mixture is cooled to room temperature, 17.2 g (0.2 mole) of methacrylic acid and 18.1 g (0.1 mole) of 4-nitrophenylacetic acid are added to the solution, and the reaction is stirred at room temperature for 3 hours. The mixture then is heated at reflux for 16 hours. After cooling to room temperature, the solid diphenylbutadiene precipitates from solution and is collected by filtration and purified by recrystallization from ethanol.

Quelle